


Will that be all, sir?

by Harleythegeekqueen



Category: SPN, Supernatural
Genre: Angst, F/M, Language, Office AU, Smut, homophobic slur, plus size reader
Language: English
Status: Completed
Published: 2017-07-29
Updated: 2017-07-29
Packaged: 2018-12-08 09:44:08
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,314
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11643933
Author URL: https://archiveofourown.org/users/Harleythegeekqueen/pseuds/Harleythegeekqueen
Summary: After a disastrous morning trying to get coffee for your boss, and a jerk making fun of your size you’re dismayed to find said jerk in your boss’ office when you arrive. Thankfully Mr. Winchester is very understanding and knows how to make you feel better.





	Will that be all, sir?

**Author's Note:**

> I think this was the coolest idea for a challenge. One prompt and so many possibilities! You’re a rockstar @@impala-dreamer . [Here](https://impala-dreamer.tumblr.com/post/162546860645/impala-dreamers-one-prompt-for-all-dean) is the challenge for more information. 
> 
> I had fun with this prompt and I set up this AU a little while back and thought it fit perfectly. Please let me know if I need to add any warnings and thank you so much for reading!

  I stood quietly in the coffee line rechecking my work email for the fifth time since arriving at the coffee shop. The holiday shoppers had turned out in droves and I had overslept meaning I’d be late to work for sure. I hoped Mr. Winchester would understand but getting him a muffin would probably help matters.

  “Now there’s my space Queen,” Charlie my bubbly redheaded barista friend burst waving me up to the groans of those around me still waiting. I shook my head as the embarrassment of attention lit up my face but she was persistent. “Oh ignore them gorgeous I got your order ready anyway.”

  I moved up pulling money out, “I’ll need a chocolate chip muffin for him too today please.”

  Charlie turned to grab the muffin as the man behind me sneered, “Like you need a muffin fat ass.” Charlie turned with the drink tray and muffin in the cup holder and she sat it down before pointing her finger at the man behind me.

  “Charlie, don’t!” I begged but she shushed me and returned her attention to the man, “Listen here you dick you don’t talk about a lady like that and stay in my shop get the hell out.”

   “Charlie!” I begged and the man pushed past me.

   “Now you listen here I’m one of Chicago’s top litigators and I will talk any way I damn well please.”

    “Not here and not to her! Now I repeat, get the hell out!”

   I looked between the two trying to defuse the situation I knew how upset Charlie could get, “Charlie, it’s okay honey I hear it all the time I’m not mad.”

   “See she’s fine she knows she needs to work on her weight. Now I want to see your manager.”

   “Okay buddy,” Charlie smiled and you laughed to yourself knowing she had won. “Dorothy!”

   “Dude no offense taken but you’ve lost you should leave,” I offered.

   “Not until I speak to the manager. I’ll have her job and don’t think I don’t know who you are I’ll speak with Dean Winchester about you as well.”

   I swallowed, “What? I didn’t do anything to you. You were the one being cruel.”

  “I can’t help your dyke girlfriend is the one who did this?”

   Charlie looked over handing you the tray, “Y/N get on to work we’ll handle this and he won’t say a word to Winchester.”

    I took the tray as Dorothy appeared looking like she was ready to fight, “Hey Y/N, now as for you dick.” Dorothy put her arm around Charlie, “As appealing as Y/N is I’m the dyke girlfriend you should worry about. I also own this place and you sir are banned from ever stepping foot in here again. Now get the fuck out!”

    The man grew ever redder in the face and turned knocking my trap spilling the coffee all over me and disappearing out the door. The other customers who had witnessed rushed forward with napkins trying to help and offered encouraging words. I was nearly in tears as Charlie remade my order and Dorothy came around helping to clean up the mess.

   “I’m so sorry Y/N. Do you have time to run home and change?”

   I shook my head, “No I’m already late. Luckily I’m in all black I’ll just smell like coffee all day. I’m sorry about all this.”

   “Not your fault sugar,” Dorothy offered handing the tray she took from Charlie. “You still in for drinks with the gang tomorrow night?”

   “If Mr. Winchester doesn’t kill me for being late then yes I’ll be there. See you, girls!” I offered as I quickly ran out the door as Charlie and Dorothy yelled good luck as I made my way to the office.

    Twenty minutes later the elevator pinged to my floor and I rushed to my desk throwing my purse down and putting my coffee down checking Dean’s coffee and muffin before knocking. I heard a faint  _come in_  and opened the door carrying the tray and nearly dropped it to see the lawyer from the coffee shop sitting in the chair opposite Mr. Winchester. The man sent me a knowing smirk as Dean looked up.

   “Miss Y/L/N so glad you could make it this morning,” Dean’s tone was unnerving but you had been late and you nodded sitting down his coffee and muffin. Dean caught your eye, “Do you have anything to say for yourself?”

   “No sir it was entirely my fault and it won’t happen again,” I offered shrinking back clasping my hands in front of my still wet dress and looking down trying to not actually cry.

    “Zachariah here tells me that you had a rather unfortunate encounter at the coffee place this morning and that you were rude. Is that true?”

   I looked up to find Zachariah looking at me with a near shit eating grin and I swallowed, “I’m sorry sir.”

  Dean stands and makes a point to look me right in the eye, “You know Zachariah, Y/N is one of the finest employees I have ever had the pleasure of working with. Hardworking, dependable, trustworthy, and the list goes on. However, I can’t seem to recall her ever being rude to anyone on staff and trust me she catches a lot of shit in her position.” I swallow as he turns to Zachariah, “So perhaps next time you think it’s okay to make derogatory comments about her weight you will keep your mouth shut.”

  I freeze as Zachariah jumps up the horrible shade of red across his face replacing his smirk, “Now Mr. Winchester you see here.” Dean held up his hand successfully silencing the lawyer. Dean turned to me with a smile, “Miss Y/L/N that will be all for now. I’ll be meeting with Mr. Zachariah for a bit so please no calls.”

  “Yes sir,” I nod backing away shutting the door behind me. I had no idea how Dean knew what had actually happened but I was elated how he had defended me.

  I moved to my desk beginning to work as my phone beeped with a message from Charlie:

> _**Did I forget to mention that your boss and I are old friends?_
> 
> **You and Dean?
> 
> _**We went to college together. I’ll explain everything over drinks._ _J_
> 
> **You rock, Charlie!

    I set about responding to my emails as I look up Zachariah is walking past my desk without so much as I look in my direction as my phone beeps. “Miss Y/L/N, will you come into my office please.” Mr. Winchester sounds indifferent as I forward my phones to the main secretary Kevin and head into to his office.

    “Mr. Winchester,” I knock opening the door. Mr. Winchester is standing behind his large desk looking out the window.  

    “Come in and close the door Miss Y/L/N,” he orders and I listen crossing to his desk and sitting in one of the chairs waiting for him. Dean turns and walks around leaning against the desk in front of me. “Did you forward your phones to Kevin?”

    “Yes sir,” I answer.

    He smirks, “Good.” I smile as Dean’s on me his lips attacking mine as he pulls me up into his arms trailing kisses down my neck as his hand works the zipper on the back of my dress. “You smell like coffee.”

    “You can think that dickhead Zachariah,” I gasp as he bites into my neck before sucking at the spot. “No marks Dean.  **If I didn’t know any better I’d think you were trying to kill me.** ”

    “No Princess,” he chuckles. “Consume you perhaps. Let’s get this dress off you.” Dean pulls the dress off and holds my hand as I step out of it. “Zachariah is an absolute idiot for speaking such nasty things about you.”

    “He’s one of many Dean it’s okay,” I offer but that only seems to upset him. He takes my face into his hands and presses soft kisses to my cheeks and lips before slowly sliding down peppering every bit of exposed flesh he can find. As he reaches my stomach his thumbs hook into the edge of my panties pulling them down as he trails kisses down my left leg and back up the right before standing to wrap his arms around me. “As nice as this is Mr. Winchester you have a meeting in forty minutes.”

    “I’ll just have to be quick then,” he pushes me to the edge of his desk as he drops his pants taking his cock in hand. “Yeah, he’s a definite fucking idiot. Remember baby we have to be quiet.” I nod as he teasingly runs his cock through my folds, “You are always so wet for me.”

     “Stop teasing Winchester,” I demand through clenched lips as he slowly presses into me. I bite my lip to stifle the moan as he bottoms out and stops moving. His right-hand moves to cradle the back of my head as the left squeezes my hips as he slowly begins moving back and forth. “Dean.”

     Sweat beads along his forehead as he picks up the pace. I run my hands up his arms as the warm tingling of an orgasm begins to build, “Baby I’m so close.” He grunts as the paces quickens to a near brutal cadence and I know  I’ll be bruised but it’s not the first time and it’s always worth just to be with Dean. This started months ago it was usually just all physical, but today feels different. Not to mention the way Dean is looking at me screams it’s different. His hand releases my hip moving up to cup my breast as he drags his mouth down nipping through the lace at my nipple. It lasts for a few minutes as he goes back and forth between my breasts before his hand trails down between my legs his thumb circling my clit, “Come with me, sweetheart.”

     “D..Dean f…f…fuck,” I gasp as Dean explodes inside me and pulls my orgasm from me, my nails digging into his shoulders. His lips find mine again and he kisses me like a man in desperation. “I wish people would make fun of me more often.”

     “Alright smart-ass,” Dean stands to help me to the chair while he disappears into the small hidden bathroom of his office. He comes back with a cloth and a tube of makeup. “For your neck, I got carried away. I’m sorry,” Dean has always been an excellent caregiver after sex. I took the makeup and allow him to direct me as to where it’s needed. He takes it back to the restroom as I pull my underwear back on and step back into my dress.

      “Mind zipping me up boss?” Dean comes over and does as I ask before turning me and kissing me once more. “You keep that up and you’ll miss your meeting.”

      I joke but when I look up Dean’s face has fallen and he looks torn between angry and sad once more. Unsure of what to do I pick up his hand place a kiss on his palm and hold it to my cheek, “I’m okay Winchester he’s just another dickhead in a long list of dickheads." 

      “Would you have told me what happened if he hadn’t and you walked in here seeing him?”

      “No probably not because I know it would only upset you. I’ve heard that and worse since I was a kid Charlie can tell you, which by the way we need to talk about. I had no idea you knew Charlie!”

       He chuckles lightly squeezing my cheek before moving his hand down to take mine in his. He kisses my palm as I did him but instead of his face he places it over his heart, "How about I tell you about it tonight over dinner at my place?”

       Dean’s searching my face for answers but I’m kind of surprised. The arrangement was simple we relieved  _stress_  from work on each other and we don’t talk about it outside of his office. Not that I’m opposed to something more it’s Dean after all and I’m pretty certain that I’d follow this man into battle if it was a call for, "You really are trying to kill me aren’t you?”

       “Have you ever considered that maybe you’re killing me?” I laugh tapping his chest as he continues, “Seriously, though I just want to spend time with you outside of these four walls. Have dinner with me I’ll even send Benny to get you.”

       "Are you sure you want this Dean? I mean I’ve wanted more since we started this, but we haven’t talked beyond the sex. I don’t want to lose what we have if you decide you don’t want me later,” despite generally being positive old insecurities surface time to time. Plus you’d rather have Dean like this than not at all.

        Dean pulls me into his chest leaning down into my ear, “I’ve wanted this for a while I was just afraid.”

       "Okay,“ I pull back kissing his nose. "I’ll patiently await Benny’s escort then. Let’s say six o’clock?”

        He nods at me with a smile and I turn heading for the door. Poor Kevin is probably losing his mind right now, "Oh, and Y/N?" 

         I turn back to Dean as he scratches the back of his head nervously, "It’s Friday night so maybe bring an overnight bag. You know in case you want dessert or breakfast.” 

       "Yes sir,” I wink with a smile that now mirrors his own. “Will that be all Mr. Winchester?" 

      "Yes, Miss Y/L/N, for now,” I giggle and closed his door behind me taking a deep breath. All in all, despite smelling like a Starbucks this has turned into a perfect Friday. 


End file.
